Palladium‐catalyzed amination with benzophenone imine as a new, safe and practical alternative to nitration for the synthesis of 7‐amino‐2,1,3‐benzothiadiazoles

Abstract

AbstractPalladium‐catalyzed amination of 7‐bromo‐4‐methyl‐2,1,3‐benzothiadiazole (7) with benzophenone imine as an ammonia equivalent is described as a new, safe and practical alternative to nitration for the synthesis of 7‐amino‐4‐methyl‐2,1,3‐benzothiadiazole (1) in high yield. This methodology was successfully scaled‐up in the pilot plant on 14.0‐kg scale of 7 and was also utilized for the synthesis of 7‐amino‐4,6‐dimethyl‐2,1,3‐ben‐zothiadiazole (12) by the amination of 7‐bromo‐4,6‐dimethyl‐2,1,3‐benzothiadiazole (10).